WO2008115934A1 - Procédés pour générer des microfibres non-cellulose comprenant un ingrédient actif - Google Patents

Procédés pour générer des microfibres non-cellulose comprenant un ingrédient actif Download PDF

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Publication number
WO2008115934A1
WO2008115934A1 PCT/US2008/057389 US2008057389W WO2008115934A1 WO 2008115934 A1 WO2008115934 A1 WO 2008115934A1 US 2008057389 W US2008057389 W US 2008057389W WO 2008115934 A1 WO2008115934 A1 WO 2008115934A1
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Prior art keywords
active ingredient
cellulose
paper
solvent
monomers
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PCT/US2008/057389
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English (en)
Inventor
Jeffrey Fowler
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Syngenta Participations Ag
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Publication of WO2008115934A1 publication Critical patent/WO2008115934A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D01F1/103—Agents inhibiting growth of microorganisms
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/38—Formation of filaments, threads, or the like during polymerisation
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/40—Formation of filaments, threads, or the like by applying a shearing force to a dispersion or solution of filament formable polymers, e.g. by stirring
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H15/00—Pulp or paper, comprising fibres or web-forming material characterised by features other than their chemical constitution
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents

Definitions

  • the present invention relates to methods for generating non cellulose microfibres which comprise an active ingredient.
  • the invention also relates to the use of such microfibres in a method of manufacturing a material which, in particular, comprises cellulose. More specifically the active ingredient is a fungicide and the material is paper.
  • Materials which comprise cellulose, such as paper, are particularly prone to fungal attack since the cellulose acts as a carbon based nutrient source. Such fungal attack often leads to degradation of the material which in turn can result in loss of mechanical properties. Growth of fungi on cellulose containing materials also leads to staining often accompanied by unpleasant smells. This can significantly affect the appearance of the material and can lead to an increased requirement for maintenance requiring much effort and expense.
  • the present invention is directed towards, inter alia, providing solutions to the problems which exist in the art.
  • a method for generating non cellulose micro fibres comprising an active ingredient comprising: (a) generating a solution (1) which comprises dissolved polymer and/or polymerisable or cross-linkable monomers and dissolved and/or dispersed active ingredient in a first solvent; and (b) adding said solution to a further solvent or mixture of solvents (2) wherein said polymer, monomers and said active ingredient are substantially insoluble in said further solvent or mixture of solvents; and (c) precipitating the polymer and optionally the monomers from the solution wherein said active ingredient is substantially confined within the precipitate.
  • the method of the present invention includes a variation wherein in step (b) the solvent is added to the solution rather than the solution added to the solvent.
  • the solvent and further solvent according to the invention are fully miscible and a solute or surfactant may be present in said further solvent in order to achieve the requisite miscibility and polymer wettability as described below, all of which will be apparent to the person skilled in the art.
  • the method of adding the solution to the solvent or mixture of solvents is performed by continuously injecting a jet or stream of the solution into a stirred vessel or flow stream of the solvent or mixture of solvents, such that the precipitated polymer and optionally monomers and said active ingredient forms into solid particles of high aspect ratio.
  • Microfibre means a, rod-like fibre which has a length of between about 0.1 to 5000 microns and will have a generally circular or elliptical cross section and/or blunt ends.
  • the synthetic micro fibres of the invention may be made of, for example, epoxy resin; polyacrylate or derivatives; vinyl; polyester; polyurethane; polyurea; polythene; polyethylene; polypropylene or any other like polymer that would be considered suitable by the person skilled in the art.
  • the microfibres may be polymer-based, monomer-based or non-crystalline based.
  • epoxy resin SU-8 is dissolved in a solvent such as ethyl lactate. Following addition of the active ingredient to this solution it may be added to a further solvent which comprises glycerin.
  • polymethymethacrylate is dissolved in a solvent such as acetone.
  • a solvent such as acetone.
  • the active ingredient may be added to a further solvent which comprises water, which may additionally contain surfactants.
  • the polymer and/or polymerisable or cross-linkable monomers are dissolved into the solution such that the dissolved polymer and/or polymerisable or cross-linkable monomers form at least about 1% of the solution. In a further embodiment, the dissolved polymer and/or polymerisable or cross-linkable monomers form at least about 10% of the solution. In a still further embodiment the dissolved polymer and/or polymerisable or cross-linkable monomers form at least about more than 10% of the solution.
  • the present invention further provides a method as described above wherein at least 75% of the active ingredient is confined within the precipitate. In a further embodiment at least 80% of the active ingredient is confined within the precipitate. In a further embodiment at least 85% of the active ingredient is confined within the precipitate. In a further embodiment at least 90% of the active ingredient is confined within the precipitate. In a further embodiment at least 95% of the active ingredient is confined within the precipitate.
  • the present invention still further provides a method as described above wherein the precipitate is constituted substantially by polymerised monomers.
  • the present invention still further provides a method as described above wherein polymerisation of the monomers in the micro fibres is further facilitated via UV light and/or reaction at elevated temperature. - A -
  • the present invention still further provides a method as described above wherein a polyfunctional amine is added to further facilitate polymerisation of said monomers in the microfibres.
  • a polyfunctional amine is added to further facilitate polymerisation of said monomers in the microfibres.
  • said amine is added to the further solvent or mixture of solvents.
  • the present invention still further provides a method as described above wherein said further solvent or mixture of solvents further facilitates polymerisation of said monomers in the microfibres.
  • a method for generating non cellulose microfibres comprising an active ingredient said method comprising (a) generating a solution (1) by dissolving and/or dispersing an active ingredient in a first solvent which comprises dissolved polymer and/or polymerisable or cross-linkable monomers; (b) combining said solution with a further solvent or mixture of solvents (2) to produce a further solution wherein said polymer and monomers and said active ingredient are substantially insoluble in said further solvent or mixture of solvents; (c) precipitating said polymer and optionally the monomers into microfibres which confine said active ingredient.
  • the solution may be combined with a further solvent or mixture of solvents by simply pouring the former into the latter, or by injecting the former into the latter through a tube having an opening below the surface of the liquid, and where the solvent or mixture of solvents is swept past the addition point such that the incoming stream of solution is subjected to extensional flow deformation, for example via a pump or an electronic rotary mixing device, such as a mechanical stirrer.
  • a pump or an electronic rotary mixing device such as a mechanical stirrer.
  • the solution (1) and the solvent or mixture of solvents (2) can also be mixed via mixing methods well known to the person skilled in the art.
  • the invention provides a method as described herein wherein solution (1) is injected into the solvent or mixture of solvents (2) or vice versa.
  • solution (1) is injected into the solvent or mixture of solvents
  • the interfacial tension between said polymer and said further solvent is sufficient to ensure that once formed the microf ⁇ bres retain an average length from about 0.1 microns to about 5000 microns.
  • said fibres are from about 1 micron to about 5000 microns in length.
  • said fibres are from about 100 micron to about 5000 microns in length.
  • said fibres are from about 500 micron to about 5000 microns in length.
  • the contact angle of the further solvent wetting said micro fiber is less than or equal to about 90°. In a further embodiment said contact angle is less than or equal to about 70°. In a still further embodiment said contact angle is less than or equal to about 50°. In a still further embodiment said contact angle is less than 50°.
  • the micro fibre it is wetted via contact with the further solvent within the solution in which the fibre is formed. If the micro fibre forms contact with the further solvent via an angle as described above the microf ⁇ bre is capable of retaining the rod- like shape for a greater period of time and is therefore more stable.
  • the person skilled in the art is capable of selecting an appropriate combination of dissolved polymer and further solvent such that upon precipitation and formation of the microf ⁇ bre, the contact angle as mentioned above is achieved.
  • the present invention still further provides a method as described above wherein the first solvent and further solvent are fully miscible.
  • micro fibres are harvested from said further solution.
  • non-cellulose active ingredient containing microfibres according to the invention may also be generated via other methods which are known in the art for the generation of the microfibres per se, wherein such prior art methods are modified to allow for the inclusion of the active ingredient so that the active ingredient becomes incorporated in the microf ⁇ bre.
  • Examples of alternative microf ⁇ bre synthesis methods include, electro spinning which is well known to the person skilled in the art.
  • the microf ⁇ bres may be generated via dissolving and/or dispersing the active ingredient in a polymer melt.
  • the active ingredient containing melt may then be emulsified via a conventional means, (such as surfactant stabilised, colloidally stabilised or maintained temporarily via mechanical agitation), into a heated further solvent. Whilst the emulsion is subjected to an extensional flow deformation, it is cooled below the solidification temperature of the polymer such that the stretched droplets form solid micro fibres. This method obviates the need to dissolve or disperse the active ingredient in a solvent as per the method described above.
  • a still further method to generate the microfibres involves dissolving and/or dispersing the active ingredient in a solution which comprises monomers which can be subsequently cross-linked into polymer.
  • the solution may be stirred into water which optionally contains a solute and the solution may be emulsified using emulsif ⁇ ers known to the person skilled in the art.
  • the resulting emulsion may then be subjected to an extensional flow deformation wherein the monomers may be cross-linked to form the solid microfibres.
  • Such cross-linking may be achieved via the methods well known in the art and applicable to the monomers used in the method.
  • a method for manufacturing a material which comprises cellulose which material additionally comprises non cellulose microfibres comprising an active ingredient comprising: (a) generating non cellulose microfibres which comprise an active ingredient and
  • microfibres to a material which comprises cellulose.
  • the microfibres may also be added to other materials such as paper, wood and other like cellulose containing items.
  • a method of preventing or reducing fungal infestation of a material comprising cellulose comprising the steps of: (a) generating non cellulose microfibres which comprise a fungicide; and (b) adding said microfibres to a material comprising cellulose.
  • a method for increasing the retention of an active ingredient in a material which comprises cellulose comprising providing non cellulose microfibres which comprise said ingredient and adding said microfibres to said material or a precursor thereof.
  • microfibres containing the active ingredient may be generated as described in this specification.
  • the present invention still further provides a method as described above wherein said active ingredient is selected from the group consisting of: fungicide, herbicide, insecticide, molluscicide; arachnidicide; nematicide, bactericide and viricide.
  • said ingredient is a fungicide.
  • said fungicide comprises a strobilurin or a strobilurin type fungicide.
  • Strobilurin and strobilurin-type fungicides are a well-known class of fungicides that act by inhibiting mitochondrial respiration by blocking electron transfer between cytochrome b and cytochrome C 1 at the ubiquinol oxidising site. They include the methoxyacrylate strobilurins such as azoxystrobin and picoxystrobin, the oximinoacetate strobilurins such as kresoxim-methyl and trifloxystrobin, the oximinoacetamide strobilurins such as dimoxystrobin, metominostrobin, orysastrobin (BAS 520) and the strobilurin of the formula:
  • dihydrodioxazine strobilurins such as fluoxastrobin, the methoxycarbamate strobilurins such as pyraclostrobin, the strobilurin of the formula:
  • Azoxystrobin is also described as entry 47 in The Pesticide Manual, Thirteenth Edition, published by The British Crop Protection Council, 2003. Picoxystrobin is also described in the Pesticide Manual as entry 647.
  • said fungicide is selected from the group consisting of: Azoxystrobin; Thiabendazole; Fludioxonil and a mixture thereof.
  • Fludioxonil is listed as entry 368
  • the Pesticide Manual, Fludioxonil is mainly known as a fungicide for use on crops and also as a seed treatment.
  • Thiabendazole is listed as entry 790.
  • said azoxystrobin, thiabendazole and fludioxonil are present in amounts which provide a synergistic effect.
  • said azoxystrobin and thiabendazole are present in amounts which provide a synergistic effect.
  • a micro fibre which comprises a fungicidally effective amount of (a) a strobilurin or strobilurin-type fungicide and (b) a fungicide selected from the group consisting of: (bi) thiabendazole; (bii) fludioxonil or a combination thereof, wherein the fungicides are present in synergistic amounts.
  • said strobilurin fungicide is azoxystrobin.
  • the microfibres according to the invention may comprise a single active ingredient or a combination of active ingredients. Where the fibres contain a single active ingredient, they may be mixed with other microfibres containing a different active ingredient to generate a mixture of fibres containing the different active ingredients.
  • the microfibres may be combined with one or more additives to improve particular properties (for example distribution on surfaces). Such additives are well known to the person skilled in the art. These may be blended with other bio-enhancing adjuvants (ingredients which may aid or modify the action of the active ingredient used in the micro fibres of the invention).
  • fungicides examples include:
  • AC 382042 N-(I -cyano-l,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide), acibenzolar-S-methyl, alanycarb, aldimorph, anilazine, azaconazole, azafenidin, benalaxyl, benomyl, benthiavalicarb, biloxazol, bitertanol, blasticidin S, boscalid (new name for nicobifen), bromuconazole, Bronopol, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA 41396, CGA 41397, chinomethionate, chlorbenzthiazone, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquino- late, copper sulphate, copper
  • insecticides which may be used in accordance with the present invention include: a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cycl opropane carboxylate; b) Organophosphates, such as, profenofos, sulf
  • Chloronicotinyl compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram or thiamethoxam;
  • Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide;
  • Diphenyl ethers such as diofenolan or pyriproxifen; o) Indoxacarb;
  • Chlorfenapyr q) Pymetrozine; r) Spirotetramat, Spiromesifen; or s) Flubendiamid or Rynaxypyr.
  • MCPB mecoprop; mecoprop-P; mefenacet; mefenpyr diethyl; mefluidide; mesosulfuron methyl; mesotrione; metam; metamifop (mefluoxafop); metamitron; metazachlor; methabenzthiazuron; methazole; methyl isothiocyanate; methylarsonic acid; methyldymron; metobenzuron; metobromuron; metolachlor; metosulam; metoxuron; metribuzin; metsulfuron-methyl; MK-616; molinate; mono linuron; MSMA; naproanilide; napropamide; naptalam; NDA-402989; neburon; nefenacet; nicosulfuron; nipyraclofen; n-methyl-glyphosate; nonanoic acid; norflurazon; oleic
  • the present invention still further provides a method of reducing the amount of an active ingredient in effluent generated during the manufacturing process of a material comprising cellulose, the manufacturing process comprising the steps of: (a) adding an active ingredient to the process water; (b) mixing said process water with said material; (c) allowing the active ingredient to associate with said material; (d) extracting the process water from the resulting material; characterised in that the active ingredient is associated with a non cellulose microfibre.
  • incorporation of the micro fibres into the material means that less active ingredient remains in the process water.
  • the present invention still further provides a method as described above wherein said material is paper.
  • the present invention still further provides a method as described above wherein some of said microfibres connect to form a fibrous mesh.
  • the present invention still further provides a method as described above wherein said microfibres are substantially rod shaped.
  • the present invention still further provides a method as described above wherein said microfibres are added to at least the top ply of the paper during the paper manufacturing process.
  • said microfibres are in at least the top and second plies of the paper.
  • said microfibres are in each of the plies of the paper.
  • the present invention still further provides a method as described above wherein said microfibres are added to at least one of the following systems or process intermediates: the thick stock; the thin stock; the water supply; the papermaking stock tank; pulp refiner; stock chest; flow box; furnish and wet-lap during the papermaking process.
  • the microfibres according to the invention may be added to any convenient stage and time during the paper making process.
  • the present invention still further provides a material comprising cellulose which material additionally comprises non cellulose microfibres which comprise an active ingredient.
  • said ingredient is a fungicide.
  • said material is paper.
  • the present invention still further provides paper containing non-cellulosic microfibres which comprise a fungicidally active compound.
  • said fungicide is selected from the group consisting of: Azoxystrobin; Thiabendazole; Fludioxonil and a mixture thereof.
  • said paper comprises Azoxystrobin and Thiabendazole.
  • said paper comprises Azoxystrobin, Thiabendazole and Fludioxonil.
  • the present invention still further provides a wallboard comprising paper as described above.
  • Wallboard also sometimes known as drywall or plasterboard
  • Wallboard includes ceiling board which is material used for internal ceilings.
  • Wallboard is generally in the form of a flat sheet between 0.5 and 2 cm thick and comprises, usually, a gypsum core, usually coated on both sides, with paper.
  • Wallboard is usually fixed to a wooden frame to form an internal wall, or fixed to ceiling spars to form an internal ceiling.
  • Wallboard has many desirable properties, such as being relatively light and easy to cut, and having a surface that is easily decorated with paint or wallpaper.
  • the microfibres according to the invention may be included in the paper of the wallboard, in the core of the wallboard, such as the gypsum core or both the paper and the core.
  • the fungicide/fungicides is/are present (within the microfibres) in the wallboard or paper coating in concentrations of about 50ppm to 5000ppm, more preferably from 1100 to 1300ppm in the paper.
  • the present invention still further provides a building comprising a wallboard as described above.
  • said building is a temporary building.
  • said building is a permanent structure.
  • said building comprises a plurality of wallboards as described above.
  • compositions for use in a method as described above which composition comprises a dispersion of non cellulose microfibres which comprise an active ingredient in a liquid.
  • liquid is water.
  • the present invention still further provides a fibrous mesh which comprises non cellulose microfibres which comprise an active ingredient.
  • said ingredient is a fungicide.
  • the present invention still further provides the use of a non cellulose micro fibre which comprises an active ingredient in the manufacture of a material which comprises cellulose. In a particular embodiment said micro fibre is used in the manufacture of paper.
  • micro fibres of the invention which contain a fungicide may be used in the prevention and/or treatment of growth of a number of fungi including the following: Alternaria alternata, Aspergillus flavus, Aspergillus terreus, Aspergillus fumigatus, Aspergillus repens, Aspergillus versicolor, Candida albicans, Chaetomium globosum, Cladosporium cladosporioides, Cladosporium herbarum, Cladosporium sphaerospermum, Coniophora souna, Curvularia genticulata, Diplodia natalensis, Epidermophyton floccosum, Fusarium oxysporum, Gliocladium virens, Gloeophyllum trabeum, Humicola grisea, Lecythophora mutabilis, Lentinus cyathiformis, Lentinus lepidus, Memnionella
  • microfibres containing a fungicide for incorporation into a material which fungicides are effective against the following fungi: Alternaria alternata, Alternaria tenuissima, Aspergillus niger, Aspergillus versicolor, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Coniophora souna, Gloeophyllum trabeum, Memnionella echinata, Mucor indicus, Oligoporus placenta, Penicillium citrinum, Penicillium chrysogenum, Penicillium funiculosum, Penicillium pinophilum, Sclerophoma phytiophila, Stachybotrys atra, Stachybotrys chartarum, and Ulocladium chartarum.
  • the invention will now be described with reference to the following examples:
  • a laboratory hand sheet sample was prepared using a conventional Britt jar by adding
  • microfibre suspension prepared according to the method of example 1.
  • the effluent collected during formation of the hand sheet contained no detectable residue ( ⁇ 0.5 ppm) of the three active ingredients present in the microfibre suspension.
  • the hand sheet was inoculated with stock cultures of Aspergillus niger (ATCC6275), Stachybotrys chartarum (ATCC 16026), Penicillium citrinum (ATCC 9849) and Chaetomium globosum (ATCC 6205), then placed in an incubation chamber. After 4 weeks there was no detectable mould growth.
  • Example 3 (water-based solvent system) 2 g of polymethylmethacrylate was dissolved in 18 g of acetone. To this solution was added 0.2 g each of thiabendazole and azoxystrobin, and 0.02 g of fludioxonil. A microfibre suspension was prepared by adding 20 g of this suspension to 1500 mL of water under vigorous agitation.
  • a microfibre preparation prepared according to the method of example 3 was concentrated by vacuum filtration on a paper filter disk in a conventional Buchner funnel.
  • the microf ⁇ bres could be re-dispersed into an aqueous dispersion by stirring the filter cake vigorously into water.
  • Example 6 generation of microfibres by injecting a jet of fluid into extensional flow deformation
  • 7.6 g of epoxy resin SU-8 was dissolved in 11.5 g of gamma butyrolactone.
  • To this solution were added 0.56g of azoxystrobin, 0.11 g of fludioxonil and 0.56 g of chlorothalonil.
  • the first two active ingredients went fully into solution while the latter active ingredient remained partly as a fine particulate suspension, which upon warming was only slightly turbid.
  • a micro fibre suspension was prepared by adding 0.81 g of this solution to 61 g of propylene glycol.
  • the addition was performed by pumping the solution through a tube ending in a hypodermic needle placed below the surface of the propylene glycol, and during the addition process the propylene glycol was stirred vigorously so that the incoming solution stream was continuously stretched by the strong extensional flow deformation and the epoxy resin and active ingredients were precipitated into microfibres.

Abstract

La présente invention concerne, entre autres, des procédés pour générer des microfibres non-cellulose qui comprennent un ingrédient actif. L'invention concerne également l'utilisation de telles microfibres dans un procédé de fabrication d'un matériau qui comprend en particulier de la cellulose. Plus spécifiquement, l'ingrédient actif est un fongicide et le matériau est du papier.
PCT/US2008/057389 2007-03-19 2008-03-19 Procédés pour générer des microfibres non-cellulose comprenant un ingrédient actif WO2008115934A1 (fr)

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WO2020228238A1 (fr) * 2019-10-17 2020-11-19 深圳晶泰科技有限公司 Procédé de simulation moléculaire monte carlo à haut rendement pour calculer une tension interfaciale en phase liquide eau/benzène au moyen d'une somme ewald améliorée
CN112074595A (zh) * 2018-09-05 2020-12-11 松下知识产权经营株式会社 番茄病原性真菌的检测装置和使用该装置的检测方法
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Cited By (9)

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Publication number Priority date Publication date Assignee Title
EP2498598A1 (fr) * 2009-11-13 2012-09-19 Syngenta Participations AG Procédés de production de particules polymères à rapport d'aspect élevé comprenant un ingrédient actif
EP2498598A4 (fr) * 2009-11-13 2013-10-23 Syngenta Participations Ag Procédés de production de particules polymères à rapport d'aspect élevé comprenant un ingrédient actif
AU2010319393B2 (en) * 2009-11-13 2014-08-21 Syngenta Participations Ag Methods for generating high aspect ratio polymeric particles comprising an active ingredient
US10357030B2 (en) 2009-11-13 2019-07-23 Syngenta Participations Ag Methods for generating high aspect-ratio polymeric particles comprising an active ingredient
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